Undecanal

Last updated
Undecanal
Undecanal.svg
Names
Preferred IUPAC name
Undecanal
Other names
Undecyl aldehyde
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
DrugBank
ECHA InfoCard 100.003.611 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 203-972-6
PubChem CID
UNII
  • InChI=1S/C11H22O/c1-2-3-4-5-6-7-8-9-10-11-12/h11H,2-10H2,1H3
    Key: KMPQYAYAQWNLME-UHFFFAOYSA-N
  • InChI=1/C11H22O/c1-2-3-4-5-6-7-8-9-10-11-12/h11H,2-10H2,1H3
    Key: KMPQYAYAQWNLME-UHFFFAOYAE
  • O=CCCCCCCCCCC
Properties
C11H22O
Molar mass 170.296 g·mol−1
Appearancecolourless oil
Density 0.825 g cm−3
Melting point −2 °C (28 °F; 271 K)
Boiling point 120 to 122 °C (248 to 252 °F; 393 to 395 K)
Hazards
GHS labelling:
GHS-pictogram-exclam.svg
Warning
H315, H412
P264, P273, P280, P302+P352, P321, P332+P313, P362, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Undecanal, also known as undecyl aldehyde, is an organic compound with the chemical formula C10H21CHO. It is an eleven-carbon aldehyde. A colourless, oily liquid, undecanal is a component of perfumes. Although it occurs naturally in citrus oils, it is produced commercially by hydroformylation of decene. [1]

It has been registered under the EU REACH scheme at >1000 tonnes by Oxea, which confirms the status as irritant. [2]

Undecanal is used in the synthesis of Disparlure. [3]

Related Research Articles

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In organic chemistry, an aldol describes a structural motif consisting of a 3-hydroxy ketone, R−CH(OH)−CHR'−C(=O)−R", or 3-hydroxyaldehyde, R−CH(OH)−CHR'−CH=O. Both are composed of a hydroxy group and either a ketone or an aldehyde. An aldol consisting of a 3-hydroxy ketone is called a β-hydroxy ketone, and an aldol consisting of a 3-hydroxy aldehyde is called a β-hydroxy aldehyde. The term "aldol" may refer to 3-hydroxybutanal.

1-Hexanol (IUPAC name hexan-1-ol) is an organic alcohol with a six-carbon chain and a condensed structural formula of CH3(CH2)5OH. This colorless liquid is slightly soluble in water, but miscible with diethyl ether and ethanol. Two additional straight chain isomers of 1-hexanol, 2-hexanol and 3-hexanol, exist, both of which differing by the location of the hydroxyl group. Many isomeric alcohols have the formula C6H13OH. It is used in the perfume industry.

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<span class="mw-page-title-main">Oxazole</span> Chemical compound

Oxazole is the parent compound for a vast class of heterocyclic aromatic organic compounds. These are azoles with an oxygen and a nitrogen separated by one carbon. Oxazoles are aromatic compounds but less so than the thiazoles. Oxazole is a weak base; its conjugate acid has a pKa of 0.8, compared to 7 for imidazole.

Dimethylformamide is an organic compound with the formula (CH3)2N−C(=O)H. Commonly abbreviated as DMF, this colourless liquid is miscible with water and the majority of organic liquids. DMF is a common solvent for chemical reactions. Dimethylformamide is odorless, but technical-grade or degraded samples often have a fishy smell due to impurity of dimethylamine. Dimethylamine degradation impurities can be removed by sparging samples with an inert gas such as argon or by sonicating the samples under reduced pressure. As its name indicates, it is structurally related to formamide, having two methyl groups in the place of the two hydrogens. DMF is a polar (hydrophilic) aprotic solvent with a high boiling point. It facilitates reactions that follow polar mechanisms, such as SN2 reactions.

<span class="mw-page-title-main">Diisobutylaluminium hydride</span> Chemical compound

Diisobutylaluminium hydride (DIBALH, DIBAL, DIBAL-H or DIBAH) is a reducing agent with the formula (i-Bu2AlH)2, where i-Bu represents isobutyl (-CH2CH(CH3)2). This organoaluminium compound is a reagent in organic synthesis.

<span class="mw-page-title-main">Zinc cyanide</span> Chemical compound

Zinc cyanide is the inorganic compound with the formula Zn(CN)2. It is a white solid that is used mainly for electroplating zinc but also has more specialized applications for the synthesis of organic compounds.

In organic chemistry, a homologation reaction, also known as homologization, is any chemical reaction that converts the reactant into the next member of the homologous series. A homologous series is a group of compounds that differ by a constant unit, generally a methylene group. The reactants undergo a homologation when the number of a repeated structural unit in the molecules is increased. The most common homologation reactions increase the number of methylene units in saturated chain within the molecule. For example, the reaction of aldehydes or ketones with diazomethane or methoxymethylenetriphenylphosphine to give the next homologue in the series.

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Octanal is the organic compound, an aldehyde, with the chemical formula CH3(CH2)6CHO. A colorless fragrant liquid with a fruit-like odor, it occurs naturally in citrus oils. It is used commercially as a component in perfumes and in flavor production for the food industry. It is usually produced by hydroformylation of heptene and the dehydrogenation of 1-octanol.

Heptanal or heptanaldehyde is an alkyl aldehyde. It is a colourless liquid with a strong fruity odor, which is used as precursor to components in perfumes and lubricants.

<span class="mw-page-title-main">Phenylacetaldehyde</span> Chemical compound

Phenylacetaldehyde is an organic compound used in the synthesis of fragrances and polymers. Phenylacetaldehyde is an aldehyde that consists of acetaldehyde bearing a phenyl substituent; the parent member of the phenylacetaldehyde class of compounds. It has a role as a human metabolite, a Saccharomyces cerevisiae metabolite, an Escherichia coli metabolite and a mouse metabolite. It is an alpha-CH2-containing aldehyde and a member of phenylacetaldehydes.

2-Methylundecanal is an organic compound that is found naturally in kumquat peel oil. This compound smells herbaceous, orange, and ambergris-like. At high dilution it has a flavor similar to honey and nuts. It is a colorless or pale yellow liquid that is soluble in organic solvents such as ether and ethanol. It is used as a fragrance component in soaps, detergents, and perfumes.

Lindgren oxidation is a selective method for oxidizing aldehydes to carboxylic acids. The reaction is named after Bengt O. Lindgren.

<span class="mw-page-title-main">Sodium triacetoxyborohydride</span> Chemical compound

Sodium triacetoxyborohydride, also known as sodium triacetoxyhydroborate, commonly abbreviated STAB, is a chemical compound with the formula Na[(CH3COO)3BH]. Like other borohydrides, it is used as a reducing agent in organic synthesis. This colourless salt is prepared by protonolysis of sodium borohydride with acetic acid:

<span class="mw-page-title-main">Propargyl bromide</span> Chemical compound

Propargyl bromide, also known as 3-bromo-prop-1-yne, is an organic compound with the chemical formula HC≡CCH2Br. A colorless liquid, it is a halogenated organic compound consisting of propyne with a bromine substituent on the methyl group. It has a lachrymatory effect, like related compounds. The compound is used as a reagent in organic synthesis.

cis-7,8-Epoxy-2-methyloctadecane (also known as disparlure) is a chemical compound with formula C19H38O. It is a sex pheromone found in moths, such as the spongy moth, and is used to attract a mate. It is also a harmful pesticide for many tree species.

<span class="mw-page-title-main">Cashmeran</span> Chemical compound

Cashmeran is a chemical compound used in fragrances.

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References

  1. Christian Kohlpaintner, Markus Schulte, Jürgen Falbe, Peter Lappe, Jürgen Weber, Guido D. Frey. "Aldehydes, Aliphatic". Ullmann's Encyclopedia of Industrial Chemistry . Weinheim: Wiley-VCH. doi:10.1002/14356007.a01_321.pub3. ISBN   978-3527306732.{{cite encyclopedia}}: CS1 maint: multiple names: authors list (link)
  2. http://apps.echa.europa.eu/registered/data/dossiers/DISS-9d84f5d2-6b83-52c9-e044-00144f67d249/DISS-9d84f5d2-6b83-52c9-e044-00144f67d249_DISS-9d84f5d2-6b83-52c9-e044-00144f67d249.html [ dead link ]
  3. https://chem.libretexts.org/Bookshelves/Organic_Chemistry/Logic_of_Organic_Synthesis_(Rao)/05%3A_Strategies_in_Disparlure_Synthesis